Exploitation of Cyclopropane Carbaldehydes to Prins Cyclization: Quick Access to ( E)-Hexahydrooxonine and Octahydrocyclopenta[ b]pyran

Pankaj Kumar; Raghunath Dey; Prabal Banerjee

doi:10.1021/acs.orglett.8b02094

Exploitation of Cyclopropane Carbaldehydes to Prins Cyclization: Quick Access to ( E)-Hexahydrooxonine and Octahydrocyclopenta[ b]pyran

Org Lett. 2018 Sep 7;20(17):5163-5166. doi: 10.1021/acs.orglett.8b02094. Epub 2018 Aug 15.

Authors

Pankaj Kumar¹, Raghunath Dey¹, Prabal Banerjee¹

Affiliation

¹ Department of Chemistry , Indian Institute of Technology Ropar , Nangal Road , Rupnagar , Punjab 140001 , India.

PMID: 30110172
DOI: 10.1021/acs.orglett.8b02094

Abstract

A single-step TiX₄-mediated Prins-type cyclization of cyclopropane carbaldehydes with 3-buten-1-ol for the highly stereoselective construction of relatively strained ( E)-hexahydrooxonines is reported. Switching the alcohol to 3-butyn-1-ol prompted a similar route, augmented by another cyclization within a nine-membered ring to afford a bicyclized product (4,4-dihalo-5-aryloctahydrocyclopenta[ b]pyran). Easy transformation of the resulting geminal dihalide to a vinyl halide and a ketone further supplemented the substance of this approach.

Publication types

Research Support, Non-U.S. Gov't